Help Desk Technician Tier 2

Benefits

• 401(k) matching
• Bonus based on performance
• Company car
• Competitive salary
• Dental insurance
• Free food & snacks
• Health insurance
• Opportunity for advancement
• Paid time off
• Training & development
• Vision insurance
• Competitive compensation
• Fun, supportive workplace culture
• Pay commensurate with experience and qualifications
• Opportunities for career development and advancement
• Engaging, fast‑paced MSP environment

Job Title: Help Desk Technician – Tier 2

Full Time – In Office - Annapolis, MD

ICSI is a leading Managed Service Provider (MSP) dedicated to delivering top‑notch IT solutions to our clients. We pride ourselves on our commitment to excellence and our ability to solve complex IT challenges. Our team includes experts from ICSI, a leader in managed IT services, known for increasing IT and security maturity levels.

• Diagnose and resolve technical issues, including Microsoft core business applications and operating systems.
• Deliver comprehensive troubleshooting and backend support to end users.
• Troubleshoot and resolve complex workstation issues and provide general server support.
• Perform initial triage for network degradation, outages, compromised accounts, and other critical technical incidents.
• Support Microsoft technologies such as Windows Server, Exchange, and SharePoint.
• Maintain and update system documentation within Connect Wise and IT Glue.
• Enhance customer satisfaction through high‑quality service and support.
• Ensure compliance with all company policies and procedures.
• Carry out additional duties as assigned by the supervisor.
• Participate in the on‑call rotation during non‑business hours.

• Strong diagnostic and troubleshooting skills for a wide range of technical issues.
• Networking knowledge (DHCP, DNS, Wi‑Fi setup, VLAN concepts).
• Strong knowledge with Microsoft 365, Entra /Azure AD, and user provisioning workflows.
• Solid understanding of Windows and macOS operating systems, networking fundamentals, and common business applications.
• Excellent analytical, problem‑solving, and communication skills.
• Ability to work independently as well as collaboratively within a team.
• Relevant certifications such as CompTIA A+, Network+, or Microsoft certifications are a plus.
• Strong customer service orientation with the ability to manage multiple tasks and adapt quickly to change.
• Prior experience with Connect Wise is a plus.

• Windows Server (2012+) / Active Directory
• Windows 10 & 11
• Office 365 / Microsoft 365 / Entra
• Backup solutions:
  Datto, Veeam
• Network/security:
  Sonic Wall, Cisco Meraki
• Security platforms:
  Sentinel One, Webroot, Barracuda, Avanan
• Mobile device management:
  Intune/MDM

• Proven experience in an IT support role, preferably within an MSP environment.
• Hands‑on experience with Microsoft 365, Exchange, and Active Directory.
• Experience supporting cloud environments (Azure, AWS, Google Cloud) is a plus.
• Demonstrated ability to diagnose and resolve technical issues efficiently and professionally.

• Regular, reliable attendance
• Ability to lift and carry up to 50 lbs
• Ability to communicate clearly over the phone